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KF/clinoptilolite nanoparticles as an efficient nanocatalyst for the Strecker synthesis of α-aminonitriles

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Abstract

Potassium fluoride impregnated on clinoptilolite nanoparticles (KF/CP NPs) have been explored to serve as an effective and inexpensive heterogeneous catalyst for the one-pot three-component Strecker synthesis of a variety of α-aminonitriles at room temperature in ethanol as a green solvent. KF/CP NPs have been synthesized using simple impregnation techniques in aqueous media from readily available inexpensive starting materials and displayed its initial catalytic activity even after five runs. The easy preparation and separation of catalyst, simple procedure, mild reaction conditions, and excellent yields of products render this method as an attractive sustainable option.

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References

  1. Strecker A (1850) Ann Chem Pharm 75:27

    Google Scholar 

  2. Enders D, Shilvock JP (2000) Chem Soc Rev 29:359

    CAS  Google Scholar 

  3. Duthaler RO (1994) Tetrahedron 50:1539

    CAS  Google Scholar 

  4. Namba K, Shinada T, Teramoto T, Ohfune Y (2000) J Am Chem Soc 122:10708

    CAS  Google Scholar 

  5. Vedejs E, Kongkittingam C (2001) J Org Chem 66:7355

    CAS  PubMed  Google Scholar 

  6. Reddy R, Jaquith JB, Neelagiri VR, Saleh-Hanna S, Durst T (2002) Org Lett 4:695

    CAS  PubMed  Google Scholar 

  7. Wang L, Shen J, Tang Y, Chen Y, Wang W, Cai Z, Du Z (2007) Org Process Res Dev 11:487

    CAS  Google Scholar 

  8. Hou YL, Sun RWY, Zhou XP, Wang JH, Li D (2014) Chem Commun 50:2295

    CAS  Google Scholar 

  9. Ghafuri H, Rashidizadeh A, Ghorbani B, Talebi M (2015) New J Chem 39:4821

    CAS  Google Scholar 

  10. Pathare SP, Akamanchi KG (2012) Tetrahedron Lett 53:871

    CAS  Google Scholar 

  11. Prakash GK, Surya Thomas TE, Bychinskaya I, Prakash AG, Panja C, Vaghoo H, Olah GA (2008) Green Chem 10:1105

    CAS  Google Scholar 

  12. Indalkar K, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:2144

    CAS  Google Scholar 

  13. De Kanta S (2005) Synth Commun 35:1577

    Google Scholar 

  14. Wang W, Wang Y, Wu B, Cong R, Gao W, Qin B, Yang T (2015) Catal Commun 58:174

    CAS  Google Scholar 

  15. Sakurai R, Suzuki S, Hashimoto J, Baba M, Toh O, Uchida A, Hattori T, Miyano S, Yamaura M (2004) Org Lett 6:2241

    CAS  PubMed  Google Scholar 

  16. Yadav JS, Subba Reddy BV, Eeshwaraiah B, Srinivas M (2004) Tetrahedron 60:1767

    CAS  Google Scholar 

  17. Royer L, De SK, Gibbs RA (2005) Tetrahedron Lett 46:4595

    CAS  Google Scholar 

  18. Jarusiewicz J, Choe Y, Yoo KS, Park ChP, Jung KW (2009) J Org Chem 74:2873

    CAS  PubMed  PubMed Central  Google Scholar 

  19. Surendra K, Srilakshmi Krishnaveni N, Mahesh A, Rama Rao K (2006) J Org Chem 71:2532

    CAS  PubMed  Google Scholar 

  20. Rajabi F, Ghiassian S, Saidi MR (2010) Green Chem 12:1349

    CAS  Google Scholar 

  21. Narasimhulu M, Reddy TS, Mahesh KC, Reddy SM, Reddy AV, Venkateswarlu Y (2007) J Mol Catal A Chem 264:288

    CAS  Google Scholar 

  22. Wang W, Zhang S, Hu S, Wang D, Gao W, Cong R, Yang T, Shaabani A, Maleki A (2017) Appl Catal A Gen 542:240

    CAS  Google Scholar 

  23. Horenstein BA, Nakanishi K (1989) J Am Chem Soc 111:6242

    CAS  Google Scholar 

  24. Heydari A, Arefi A, Khaksar S, Shiroodi RK (2007) J Mol Catal A Chem 271:142

    CAS  Google Scholar 

  25. Li P, Zhang Y, Chen Z, Zhang X (2017) Tetrahedron Lett 58:1854

    CAS  Google Scholar 

  26. Zuend SJ, Coughlin MP, Lalonde MP, Jacobsen EN (2009) Nature 461:968

    CAS  PubMed  PubMed Central  Google Scholar 

  27. Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Singh S, Suresh E, Jasra RV (2008) Tetrahedron Lett 49:640

    CAS  Google Scholar 

  28. Li Z, Sun Y, Ren X, Wei P, Shi Y, Ouyang P (2007) Synlett 2007:803

    Google Scholar 

  29. Ranu BC, Dey SS, Hajra A (2002) Tetrahedron 58:2529

    CAS  Google Scholar 

  30. Yang T, Bartoszewicz A, Ju J, Sun JL, Liu Z, Zou XD, Wang YX, Li GB, Liao FH, Martín-Matute B, Lin JH (2011) Angew Chem Int Ed 50:12555

    CAS  Google Scholar 

  31. Choi J, Yang HY, Kim HJ, Son SU (2010) Angew Chem Int Ed 49:7718

    CAS  Google Scholar 

  32. Shen ZL, Ji SJ, Loh TP (2008) Tetrahedron 64:8159

    CAS  Google Scholar 

  33. Seayad AM, Ramalingam B, Chai CLL, Li CZ, Garland MV, Yoshinaga K (2012) Chem Eur J 18:5693

    CAS  PubMed  Google Scholar 

  34. De SK (2005) J Mol Catal A Chem 225:169

    CAS  Google Scholar 

  35. Dekamin MG, Azimoshan M, Ramezani L (2013) Green Chem 15:811

    CAS  Google Scholar 

  36. Liu Y, Mo K, Cui Y (2013) Inorg Chem 52:10286

    CAS  PubMed  Google Scholar 

  37. Mobaraki A, Movassagh B, Karimi B (2014) ACS Comb Sci 16:352

    CAS  PubMed  Google Scholar 

  38. Kaur B, Chand S, Malik AK, Dhaliwal KS, Younis SA, Kim KH (2019) J Clean Prod 234:329

    CAS  Google Scholar 

  39. Kouznetsov VV, Galvis CEP (2018) Tetrahedron 74:773

    CAS  Google Scholar 

  40. Niknam K, Saberi D, Nouri-Sefat M (2010) Tetrahedron Lett 51:2959

    CAS  Google Scholar 

  41. Baghery S, Zolfigol MA, Schirhagl R, Hasani M, Stuart MCA, Nagl A (2017) Appl Organomet Chem 31:e3883

    Google Scholar 

  42. Olah GA, Mathew T, Panja C, Smith K, Surya Prakash GK (2007) Catal Lett 114:1

    CAS  Google Scholar 

  43. Baeza A, Nájera C, Sansano JM (2007) Synthesis 2007:1230

    Google Scholar 

  44. Karimi B, Zareyee D (2009) J Mater Chem 19:8665

    CAS  Google Scholar 

  45. Zareyee D, Shokuhi Rad A, Ataei Z, Javadi SH, Khalilzadeh MA (2018) Appl Organomet Chem 32:e4422

    Google Scholar 

  46. Zareyee D, Ghandali MS, Khalilzadeh MA (2011) Catal Lett 141:1521

    CAS  Google Scholar 

  47. Zareyee D, Serehneh M (2014) J Mol Catal A Chem 391:88

    CAS  Google Scholar 

  48. Esfahani FK, Zareyee D, Yousefi R (2014) ChemCatChem 6:3333

    CAS  Google Scholar 

  49. Zareyee D, Moosavi SM, Alaminezhad A (2013) J Mol Catal A Chem 378:227

    CAS  Google Scholar 

  50. Zareyee D, Alizadeh H (2014) RSC Adv 4:37941

    CAS  Google Scholar 

  51. Keipour H, Hosseini A, Khalilzadeh MA, Ollevier T (2015) Lett Org Chem 12:645

    CAS  Google Scholar 

  52. Hallajian S, Khalilzadeh MA, Tajbakhsh M, Alipour E, Safaei Z (2015) Comb Chem High Throughput Screen 18:486

    CAS  PubMed  Google Scholar 

  53. Khalilzadeh MA, Hosseini A, Pilevar A (2011) Eur J Org Chem 8:1587

    Google Scholar 

  54. Khalilzadeh MA, Keipour H, Hosseini A, Zareyee D (2014) New J Chem 38:42

    CAS  Google Scholar 

  55. Salmanpour S, Khalilzadeh MA, Hosseini A (2013) Comb Chem High Throughput Screen 16:339

    CAS  PubMed  Google Scholar 

  56. Balou J, Khalilzadeh MA, Zareyee D (2017) Catal Lett 147:2612

    CAS  Google Scholar 

  57. Ando T, Yamawaki J (1979) Chem Lett 1:45

    CAS  Google Scholar 

  58. Balou J, Khalilzadeh MA, Zareyee D (2019) Sci Rep 9:3605

    PubMed  PubMed Central  Google Scholar 

  59. Sajjadi-Ghotbabadi H, Javanshir Sh, Rostami-Charati F (2016) Catal Lett 146:338

    CAS  Google Scholar 

  60. Ezzatzadeh E, Hossaini Z (2020) Mol Divers 24:81

    CAS  PubMed  Google Scholar 

  61. Smith JV (1988) Chem Rev 88:149

    CAS  Google Scholar 

  62. Ames LL (1960) Am Miner 45:689

    CAS  Google Scholar 

Download references

Acknowledgements

The authors acknowledge the Islamic Azad University of Qaemshahr Research Councils for support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran

    Razieh Oladee, Daryoush Zareyee & Mohammad A. Khalilzadeh

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  1. Razieh Oladee
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  2. Daryoush Zareyee
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  3. Mohammad A. Khalilzadeh
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Correspondence to Daryoush Zareyee.

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Oladee, R., Zareyee, D. & Khalilzadeh, M.A. KF/clinoptilolite nanoparticles as an efficient nanocatalyst for the Strecker synthesis of α-aminonitriles. Monatsh Chem 151, 611–615 (2020). https://doi.org/10.1007/s00706-020-02574-w

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